Polyterpene Compounds for Multi-Target Skin Care

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Solution Overview

Problem

The cosmetic and pharmaceutical industries seek new ingredients that can target multiple skin concerns simultaneously, such as anti-aging, volume enhancement, depigmentation, and antioxidant properties, while existing compounds like geranylgeraniol and geranylgeranyl acetone have limitations in their efficacy and range of activities.

Innovation Solution

Development of polyterpenic compounds, specifically geranyl geranyl ethyl hexanoate and geranyl geranyl octadienoate, which can be coupled with amino-acid or peptide derivatives to enhance bioavailability and penetration, offering "oleodensifying" properties, anti-oxidant, and firming effects, and used in topical compositions for skin and hair care.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If existing compounds like geranylgeraniol and geranylgeranyl acetone are used, then some skin care benefits are achieved, but their efficacy and range of activities are limited

Engineering Contradiction:
Improverange of activitiesVSAvoidefficacy
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent applies multi-functionality by designing polyterpene compounds with multiple hydrophobic chains that can simultaneously target multiple skin concerns including anti-aging, volume enhancement, depigmentation, and antioxidant protection, allowing a single compound to perform multiple functions rather than requiring separate compounds for each function

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent employs composite materials by creating polyterpene compounds composed of multiple terpene units (n=3) with specific substituents (R1, R2, R3, R4) and optional amino-acid or peptide derivatives, forming a composite molecular structure that combines the benefits of different terpene chains and bioactive moieties to achieve enhanced and diversified biological activities

Inventive Principle:
Principle #40Composite materials

2Reliability

If polyterpenic compounds with multiple hydrophobic chains are developed, then bioavailability and penetration are enhanced, but molecular complexity increases

Engineering Contradiction:
ImprovebioavailabilityVSAvoidmolecular complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by systematically varying the number of hydrophobic chains (n=3), the length and saturation of these chains (m=0 or 1, with specific carbon chain lengths), and the nature of substituents (R1, R2, R3, R4) to optimize the balance between molecular complexity and bioavailability, demonstrating that controlled parameter variation can enhance penetration while maintaining manageable complexity

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If compounds target multiple skin concerns simultaneously, then comprehensive skin care is achieved, but ingredient selection becomes more challenging

Engineering Contradiction:
Improvemulti-target capabilityVSAvoidingredient selection
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The patent applies segmentation by dividing the complex polyterpene molecule into distinct functional segments: the core polyterpene structure (providing hydrophobicity and membrane interaction), specific substituent groups (R1, R2, R3, R4) that confer different activities, and optional amino-acid or peptide derivatives that add targeted functions, allowing systematic design and selection of ingredients based on desired activities

Inventive Principle:
Principle #1Segmentation

Data Source

PatentEP2556043B1New polyterpene type compounds, compositions containing them and topical uses thereof
Publication Date: 2016.10.26 SEDERMA SA
  • EP2556043B1 patent drawing
  • EP2556043B1 patent drawing
  • EP2556043B1 patent drawing

AI summary

The compounds of the invention correspond to formula (I) with n = 0 to 5, m = 0 to 5, R1, R2 and R3, independently of each other, selected from H, an alkyl chain of 1 to 6 carbon atoms, an alcohol, alkoxy, amine and substituted amine group, and R4 selected from an alkyl, aryl, aralkyl, acyl, sugar or alkoxy chain of 1 to 6 carbon atoms, and corresponding amino-acid or peptides derivatives corresponding to the following formula (VI) (Xaa)p entity being either an amino-acid (with p=1) or any peptide having p amino-acids with p between 1 and 10. With the exclusion of the compounds corresponding in formula I to n=3, m=0, R1=H and R4=methyl or ethyl. Preferably n=3 so as to form a geranylgeranyl group. The present invention is also directed to topical compositions comprising compounds of formula I and VI. Such composition can be used in the cosmetical field to improve the overall appearance/condition of the skin and in dermo-pharmaceutical field to for preventing or treating disorders and diseases of the skin and appendages, in particular for anti aging prevention and treatment by fighting the effects of oxidation, for skin lightening, volumizing by lipofilling, and action on the mechanical skin properties.